Nu-hydrocarbyloxyalkyl-aralkylamines



United States Patent N-HYDRO CARBYLOXYALKYL-ARALKYLAMINES Alexander R. Surrey, Albany, N. Y., assignor to Sterling Drug Inc., New York, N. Y., a corporation of Delaware No Drawing. Original application February 19, 1954, Serial No. 411,554, now Patent No. 2,732,403, dated January 24, 1956. Divided and this application September 29, 1955, Serial No. 537,553

11 Claims. (Cl. 260-5709) This invention relates to N-aralkyl-N-hydrocarbyh oxyalkyl-halogenated-alkanamides and to their preparation.

The compounds of my invention have the general formula Ar-X-N where Ar is a member selected from the group consisting of phenyl, naphthyl, biphenylyl, furyl, pyridyl and thienyl radicals, X is a lower alkylene radical having one to four carbon atoms, Y is a lower alkylene radical having two to six carbon atoms and having its two free valence bonds on difierent carbon atoms, R is a hydrocarbyl radical having from one to eight carbon atoms and Ac is a lower halogenated-alkanoyl radical having one to four carbon atoms. These halogenated-alkanamides have valuable chemotherapeutic properties, for instance, amebacidal activity.

The radical Ar can have from one to three substituents such as halo, lower alkoxy, lower alkyl, lower alkylmercapto, lower alkylsulfonyl, nitro and di(lower alkyl)- amino. Furthermore, said substituents can be in any of the avaiable positions of the Ar nucleus, and where more than one substituent, they can be the same or different and can be in any of the various position combinations relative to each other. The halo substituents include chloro, bromo, iodo and fiuoro. The lower alkoxy, lower alkyl, lower alkylmercapto and lower alkylsulfonyl substituents, and the lower alkyl radicals of said di(lower alkyl)amino substituent, have preferably one to six carbon atoms, including such substituents as: methoxy, ethoxy, methylenedioxy, ethylenedioxy, n-propoxy, isopropoxy, isobutoxy, n-amoxy, n-hexoxy, and the like, when lower alkoxy; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, n-amyl, n-hexyl, and the like, when lower alkyl; methylmercapto, ethylmercapto, n-propylmercapto, isobutylmercapto, n-hexylmercapto, and the like, when lower alkylmercapto; and methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isobutylsulfonyl, n-hexylsulfonyl, and the like, when lower alkylsulfonyl; and dimethylamino, ethyl-methylamino, diisobutylamino, di-nhexylamino, and the like, when di(lower alkyl) amino.

Preferred embodiments of my invention are those N- aralkyl N hydrocarbyloxyalkyl halogenated-alkanamides where Ar is a phenyl radical as described above.

The lower alkylene radical X has one to four carbon atoms, and includes such examples as ice The lower alkylene radical Y has two to six carbon atoms and has its two free valence bonds on different carbon atoms, and includes such examples as 15 and the like.

The hydrocarbyl radical R has from one to eight carbon atoms, for instance, alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, phenyl, alkylated-phenyl, benzyl or phenethyl, and includes such examples as: methyl, ethyl, n-propyl, isopropyl, 2-butyl, isoamyl, n-hexyl, and the like, when alkyl; ethenyl, Z-propenyl, B-butenyl, 2-hexenyl, and the like, when alkenyl; cyclopropyl,--cyclobutyl, cyclopentyl, cyclohexyl, and the like, when cycloalkyl; cyclopropylmethyl, cyclopropylethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl, and the like, when cycloalkylalkyl; Z-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 3-ethylphenyl, and the like, when alkylatedphenyl.

The lower halogenated-alkanoyl radical Ac has one to four carbon atoms, and includes such examples as chloroformyl (chloromethanoyl), chloroacetyl (chloroethanoyl), iod'oacetyl, fiuoroacetyl, dichloroacetyl (dichloroethanoyl), dibromoacetyl, trichloroacetyl, 2-chloropropanoyl (alpha-chloropropionyl), 3-bromopropanoyl, 2,2- diiodopropanoyl, 2-bromo-3chloropropanoyl, 2,2-dichloropropanoyl, 2,2-difluoropropanoyl, 2,2,3-trichloropropanoyl (alpha,alpha,beta trichloropropionyl), 2-

chlorobutanoyl (alpha-chlorobutyryl), 3-bromobutanoy1,

with an acylating agent selected from the group consisting of those having the formula Ac-halogen and (Ac) O,

where Ar, X, Y, R and Ac have the meanings given above. When a halogenated-alkanoyl halide, Ac-halogen, was used, the halide halogen, i. e., the halo radical attached to the carbonyl function, was preferably chloro, however, other halo radicals, i. e., bromo, iodo and fluoro also can be used. Illustrations of the process of my invention are:

the preparation of N-(2,4-dichlorobenzyl)-N-(2-ethoxyethylJdichloroacetamide by reacting N-(2-ethoxyethyl)- 2,4-dichlorobenzylamine with dichloroacetyl chloride; the preparation of N-(2,4-dibromobenzyl)-N-(2-n-propoxypropyl)-2,3-dichloropropanamide by reacting N-(2-npropoxypropyl) 2,4 dibromobenzylamine with 2,3-dichloropropanoyl chloride; and the preparation of N-(4- nitrophenethyl) N (4 methoxybutyl)-2,2-difluorobutanamide by reacting N-(4-methoxybutyl)-4-nitrophen ethylamine with 2,2-difiuorobutanoic anhydride. When a halogenated-alkanoic anhydride is used, the reaction can be carried out at room temperature or higher if necessary. When a halogenated-alkanoyl halide was used the reaction was carried out preferably below room temperature, with chilling if necessary. In the preparation of a chloroformamide, an N hydrocarbyloxyalkyl-aralkylamine, preferably as its hydrochloride, is reacted with 0 phosgene while suspended in refluxing toluene, e. g., preparation of N-(2,4-dichlorobenzyl)-N-(2-ethoxyethyl)- chloroformamide by bubbling phosgene into a suspension 4-n-butoxybenzylamine byreacting 2=-n-butoxyethylamine with 4-n-butoxybenzaldehyde and hydrogenating the resulting anil. A third method used in preparing these intermediate N-hydrocarbyloxyalkyl-aralkylarnines was the-reaction, of anaralkylamine, ArX-NH with an lroxyal y z hali e. R-OY- aloge a. Y ntorqxy hy di mmcphenethylamine, y reacting li edi romcphe e y m n th. 2. y op p y y hlori e.

The; following examples further illustrate specific embodiments of the invention without, however, limiting t hereto EXAMPLE 1 A. Intermediate aminoethers, Ar-X-NH-YOR These intermediates were prepared by several methods, one of which is described and illustrated in this example; other-methods are presented in Examples 2A and 23. One method of preparing these aminoethers involves the reaction of an aralkylarnine, Ar-X-NH with a hydrocarbyl haloalkyl ether, R-O-Y-halide, as illustrated by the following preparation of N-(Z-ethoxyethyl)-2,4-dichlorobenzylamine: 57 g. of 2,4'-dichlorohenzylamine and 17.6 g: of 2-ethoxyethyl chloride were heated together with stirring for seven hours at 140-150 C. The reaction mixture was cooled and about 150 ml. of ether was added. The 2,4-dichlorobenzylamine hydrochloride that precipitated was filtered off and dried; weight, 32 g. (theory, 34 g.)-. The ether filtrate was evaporated in vacuo and the residue distilled under reduced pressure. There was thus obtained 21 g. ofproduct, N-(2-ethoxyethyl)-2,4-dichlorobenzylamine, B. P. 100104 C. at 0.05 mm. Hg; n =1.5208.

Analysis.Calcd. for C H Cl' NO: N; 5164. Found: N, 5 .33.

N-(2-ethoxyethyl) 2,4 dichlorobenzylamine in the form of its hydrochloride melted at 100-102" C.

Other aminoethers that were prepared following the procedure described for the preparation of N-(Z-ethoxyethyl)-2,4-dichlorobenzylamine using the appropriate reactants; are given in- Table I;

TABLE I DC H,NH OH CHO R Q R B P,O.atmm as 3,4400] 151 119-125 at 0.5 a 1. 5230 4-0 ctHq-n 0115;; 118-122 at 0. 02 b 1. 5015 400411411 CyflHB 110-175 at 0; 02 1. 5401 2,4- d1-c1 ll-CiHt. 135-140 at 0.4 1. 5147 24411-611 0113' 100-105 at 0. 4- 1; 5302 4,-0c4Ht-r OH; 134-137 at 0; 0 1. 5005. H 02H; 75 at 0. 4 1. 4985 4-OH(OH5)2 CH5 142-144 at 11-. 0 1. 4995 3401011, OH; 125-125 at 0. 1 1. 5315 3,4-(11-01 n-CrHo 144-148 at 0. 4 a 1. 5150 Other aminoethers that can be prepared according to the above procedure using the appropriate reactants include: N-(2-ethoxyethyl)-1-naphthyln1ethylam.ine, N-(2- ethoxyethyl)-1-biphenylylmethylamine, N (2 ethoxyethyl)-1-furylmethylamine, N-(Z-ethoxyethyl)-2-pyridylmethylamine, N-(2-ethoxyethyl1-4-n hexylbenzylamine, N-(Z-n-hexoxyethyl)-2,4-diiodobenzylarnine, N-( 6-methoxyhexyl) -1- 3,4-dibromopheny1) ethylamine, N- (Z-cyclohexoxyethyl) -4:-nitrophenethylamine,, N-[2 (1 propenoxy)ethyl]I-4-(3,4;5-triethoxyphenyl)butylamine, N E2 (cyclopentylmethoxy)-ethyl]-4-n-hexoxybenzylarnine, N- [Z-(Z-phenethoxy) ethyll-4-n butylsulfonylbenzylamine, and the like.

B. N-aralkyl-N-hydrocarlzyloxyalkyl-hologenatedalkanamides,

These compounds were prepared byreacting the appropriate aminoether, ArXNHY-OR, with an acylating agent selected from the group consisting of those having the formula Ac-halogen and (Ac) O. There follows an illustration of such a preparation using a hologenated-alkanoyl halide, Ac-halogen: 10 g. of dichloroacetyl chloride was added dropwise with stirring at a temperature of about 0-5" C. to 16 g. of N-(2-ethoxyethyl)-2,4-dichlorobenzy1amine in 150 ml. of ethylene dichloride and 70 ml. of 1 N sodium hydroxide. After the addition had been completed, the mixture was allowed to warm up to room temperature and stirred for another three hours. The ethylene dichloride layer was separated and washed successively with 1 N'HCI, 10% sodium carbonate solution and water. The ethylene dichloride was removed by distilling in vacuo and the residue was distilled under reduced pressure. There was obtained a fraction distilling at-134-137" C. at 0.01 mm. On standing, this fraction solidified and was recrystallized from n-hexane to give an analytically pure sample of N-(2,4-dichlorobenzyD-N-(Z ethoxyethyl)dichloroacetamide,

V P. 72.6-74.0 C. (corn).

The same product; N(2,4-dich-lorobenzyl) N 2- ethoxyethyl)dichloroacetamide, can be prepared by reacting N-(Z-ethoxyethyl)-2;4-dichlorobenzylamine with dichloroacetic anhydride instead of dichloroacetyl' chloride; In either reaction, the. N-(Z-ethoxyethyl)-2,4-dichlorobenzylamine can be used in the form of an acid addition salt; e. g., hydrochloride, by using an extra quantity of sodium hydroxide, to neutralize the liberated hydrogen chloride. This-modification. is further illustrated in Example 2B and as follows for the preparation of N (4 isopropylbenzyl) N (2-methoxyethyl)dichloroacetamide: 27 g. of N-(Z-methoxyethyl)-4-isopropylbenzylamine hydrochloride and 22 g. of dichloroacetyl chloride were placed together with 200 ml. of. benzene and refluxed for three hours with stirring. At the end of this heating period the reaction was considered complete since evolution of hydrogen chloride had ceased and the solution had become homogeneous. A small amount of methanol was added and the solvent was removed by distillation in vacuo, leaving a residue which solidified on standing. This solid was recrystallized twice from isopropanol, yielding the product, N-(4-isopropylbenzyl) N (2 methoxyethyl)dichloroacetamide, M. P. 73.7-78.5 C. (corn).

AYZGZYSLYr-Cfikld. for C15H21C12NO2: C, H, 6.65; Cl, 22.28. Found: C, 56.44; H; 6 .36; Cl, 22.0.

Other N-aralkyl N hydrocarbyloxyalkyl-halogenatedalkanamides that were prepared following theprocedure described above for the preparation of N-(ZA-dichlbrobenzyl)-N-(2-ethoxyethyl) dichloroacetamide are given in Table II.

Other N-aralkyl N hydrocarbyloxyalkyl-halogenatedalkanamides that can be prepared according to the above procedure used to prepare N-(2,4-dichlorobenzyl)-N-(2- ethoxyethyl)dichloroacetamide include the following: N- (1 naphthylmethyl) N (2 ethoxyethyl)dichloroacetamide, N-(l-biphenylylmethyl) N (2-ethoxyethyl)dichloroacetamide, N-(l-furylmethyl) N (Z-ethoxyethyl) dichloroacetamide, N-(Z-pyridylmethyl) N (2-ethoxyethyl)dichloroacetamide, N-(2,4-dichlorobenzyl) N (2- ethoxyethyl)dibromoacetamide, N-(3,4-dibromobenzyl)- N- 2-ethoxyethyl) bromochloroacetamide, N- (2,4-dichlorobenzyl -N- 2-ethoxyethyl diiodoacetarnide, N- 3,4-dichlorobenzyl) N (2-methoxyethyl)difluoroacetamide, N-(4-n-hexylbenzyl) N (Z-ethoxyethyl)-2,2-dichloropropanamide, N- (2,4-diiodobenzyl) -N- 2-n-hexoxyethyl) 2,2 diiodopropanarnide, N-[1-(3,4-dibromophenyl)ethyl] N-(6-methoxyhexyl)-2-bromo 3-chloropropanamide, N-(4-nitrophenethyl)N-(Z-cyclohexoxyethyl) 2,2,3-t1'iohloropropanamide, N- [4- 3 ,4,5triethoxyphenyl) butyl] N [2-( l-propenoxy) ethyl] -2,2-dichlorobutanamide, N- 4- n-hexoxybenzyl) N [2 (cyclopentylmethoxy)ethyl]- 3,4-dibromobutanamide, N-(4-n-butylsulfonylbenzyl)-N- [2-(2-phenethoxy) ethyl] -2,4 dibrornobutanamide, and the like.

EXAMPLE 2 A. N-(3-alkoxypr0pyl)-benzylamines A second method (see Examples 1A and 3A for other methods) for preparing the intermediate arninoethers, ArX-NHYOR, is illustrated as follows in the preparation of N-(3-ethoxypropyl)-3,4-dichlorobenzylamine: 19.5 g. of 3,4-dichlorobenzyl chloride was added dropwise with stirring to 30.9 g. of S-ethoxypropylamine. The temperature rose to a maximum of about 95 C. during the addition. stirred for an additional two hours and allowed to stand overnight. To the reaction mixture was added 35% aqueous sodium hydroxide solution and the organic layer that separated was extracted with ethylene dichloride. The extract was distilled in vacuo to remove the ethylene dichloride; the residue was dissolved in ether; and the solution was filtered. Ethanolic hydrogen chloride was added to the ether filtrate, and the solid that separated was filtered and recrystallized from ethanol. There was thus obtained 16 g. of N-(3-ethoxypropyl)- 3,4-dichlorobenzylamine as its hydrochloride, M. P.

217.1219.2 C. (corr.).

Analysis.Calcd. for C H CI NOHCI: Cl" 11.89; C, 48.26; H, 6.07. Found: Cl-, 12.13; C, 48.22; H, 6.07. Cl means ionic chlorine, i. e., chloride ion, as determined by the standard Volhard method.

Other N-(3-alkoxypropyl)-benzylamines in the form of their hydrochloride addition salts that were prepared according to the foregoing procedure are given in Table III.

F The reaction nnxture was then assase In some cases the above N-(3-alkoxypropyl)benzylamines were isolated by distillation under reduced pressure; illustrations are listed in Table IV.

TABLE IV Q Q- HPNH-GHZoHQQHT-O-R Q R B. P., C.atmm. 11,,

2,4-a1-o1 on. 132434 at o. 5 1. 5312 2,4-di-Cl CgI-Is 132-134 at; 0. 5 1. 5203 24-01-01 OH(OH 140-142 at 0. 3 1. 5170 2,4-di-Cl 110.11 146F143 at o. a 1. 5100 3,4-111-01 OH(CH3)2 135-137 at 0. 2 1. 5178 3,4-(11-01 n-C4Ho 162-165 $11: 0. 7 1. 5152 B. N-(3-alk0xypr0pyl)-N-benzyl-dichloroacetamides These compounds were prepared according to the procedure described as follows for the preparation of N-(3- ethoxypropyl) N (3,4-dichlorobenzyl)dic'hloroacetamide: 6.3 g. of dichloroacetyl chloride was added dropwise with stirring at a temperature of about 0-5 C. to 12 g. of N-(3-ethoxypropyl)-3,4-dichlorobenzylamine hydrochloride in ml. of ethylene dichloride and 88 ml. of 1 N aqueous sodium hydroxide solution. After the addition had been completed, the mixture was allowed to warm up to room temperature and stirred for an additional two to three hours. The ethylene dichloride layer was separated and washed successively with 1 N aqueous hydrochlon'c acid, 10% aqueous sodium carbonate solution and Water. The ethylene dichloride was removed by distilling in vacuo and the residue was triturated with n-hexane until solidification resulted. The solid was recrystallized once from benzene-n-pentane, twice from n-hexane and once from isopropanol-water, followed by drying at 50 C. at 20 mm. Hg for twenty-four hours.

The product thus obtained, N-(3-ethoxypropyl)-N-(3,4-

dichlorobenzyl)dichloroacetamide, melted at 60.161.8 C. (corr.).

Am1Zysis.-Calcd. for C14H1qC14NO2Z Cl, 19.01; C, 45.07; H, 4.59. Found: Cl, 18.81; C, 45.53; H, 5.01.

Other N-(3-alkoxypropyl)-N-benzyl-halogenated-acetamides prepared according to the foregoing procedure are given in Table V.

'7 EXAMPLE 3 A. N-(3-alk0xypropyl)-benzylamines A third method (see Examples 1A and 2A for other methods) of preparing the intermediate a minoethers, Ar--XNHYOR, is illustrated as follows in the preparation of N-(3-n-butoxypropyl}-4-n-butoxybenzylamine: 17.9 g. of 4-nbutoxybenzaldehyde was added to 13.2 g. of 3-n-butoxypropylamine and a solution was obtained with evolution of heat. The resulting anil was not isolated but wa-shydrogenated in absolute ethanol at room temperature with palladium chloride as the catalyst. The catalyst was filtered off and the solvent removed by distillation in vacuo. The residue was dissolved in ethyl acetate and the solution treated with ethanolic hydrogen chloride solution. The solid that precipitated was filtered and recrystallized from ethanol-ether. The product thus obtained was N-(3-bu-toxypropyl) 4 n butoxybenzylamine in the form of its hydrochloride salt, M. P. 175- 176 C.

Analysis.-Calcd. for C H NO HC1: Cl, 10.75; C, 65.53; H, 10.03. Found: Cl, 10.78; C, 65.11; H, 10.10.

Also prepared by this procedure was N-(3-methoxypropyl)-4-n-butoxybenzylamine hydrochloride, M. P. 164-165 C.

Analysis.-Calcd. for C H NO HCl: Cl, 12.32; C, 62.58; H, 9.11. Found: Cl, 12.32; C, 62.17; H, 8.98.

B. N'( S-aIkOxypropyl -N- (4-n-butoxybenzyl) dichloroacetamides EXAMPLE 4 A. N- (2-phenoxyefl1yl) -3,4-dichir0benzylanzine A mixture of 31.3 g. of 2-phenoxyethyl chloride and 70.5 g. of 3,4-dichlorobenzylamine was heated with stirring for seven hours at 140l50 C. The reaction mixture was allowed to cool and a quantity of ether was added to facilitate a separation of the 3,4-dichlorobenzylamine hydrochloride, 38 g. of which was then filtered oir' (theoretical amount is 42 g.). The ether was removed from the filtrate by distillation and the resultant heavy oil was distilled under reduced pressure, yielding the product, N-(Z-phenoxyethyl) 3,4 dichlorobenzylamine, B. P. 150-156 C. at 0.02 mm., 11 1.5755.

Analysis.Calcd. for C H Cl NO: N, 4.73. Found: N, 4.61.

N-(Z-phenoxyethyl)-3,4-dichlorobenzylamine in the form of its hydrochloride salt melted at 201-202 C.

Other N-(Z-pheuoxyethyl)-benzylamines that can be prepared according to the above procedure using the appropriate reactants include: N-(2-phenoxyethyl)-4-nbutylrnercaptobenzylamine, N-[2 (4 methylphenoxy) ethyl]-4-di-n-butylaminobenzylamine and N-[2 (4-nhexylphenoxy)ethyl]-3,4-dich1orobenzylamine.

B. N-(3,4-dichl0r0benzyl) -N-(2-phen0xyethyl) i a'ichloroacetamide To a solution containing 26 g. of N-(2-phenoxyethyl)- 3,4-dichlorobcnzylamine, 150 ml. of ethylene dichloride and 97 ml. of 1 N sodium hydroxide solution was added dropwise with stirring at about 0 to C. 13.9 g. of dichloroacetyl chloride. The reaction mixture was allowed to warm up to room temperature and was stirred for. an additional three hours. The ethylene dichloride layer 8 was separated; was washed successively with 1 N hydrochloric acid, 10% sodium carbonate solution and; water; and was dried over anhydrous calcium sulfate. The ethylene dichloride solution was then concentrated in vacuo,

, yielding a semi-solid residue which completely solidified When triturated with a small quantity of isopropanol. This solid material was recrystallized twice from isopropanol yielding the product, N-(3,4-dichlorobenzyD-N- (2-phenoxyethyl)dichloroacetarnide, M. P. 129.7-132.2 C. (corn).

Arzczlysis.Calcd. for C H ClhNO C, 50.16; H, 3.71; Cl 17.42. Found: C, 50.53; H, 3.89; Cl 17.19.

Other N-benzyl-N-(Z-phenoxyethyl) -halogenated-alkanamides that can be prepared according to the above procedure using the appropriate reactants include the following: N- 4-n-butylmercaptobenzyl) -N-(2-phenoxyethyl) 2,3,4-trichlorobutanarnide, N- 4-di-n-butylaminobenzyl) N-[2-(4 methylphenoxy) ethyl] 2,2,3 trichlorobutanamide and N-(3,4-dich1orobenzyl)-N-[2-(4-n-hexylphenoxy) cthyl] dichloroacetamide.

The N-aralkyl N hydrocarbyloxalkyl-halogenatedalkanamides of the foregoing examples when administered orally to hamsters infected with Endamoeba criceti were found to completely clear the animals at drug levels below 200 mg. per kg. of body weight. Some of the compounds, for instance, N-( 3 ,4-dich1orobenzyl) -N-(2-ethoxyethyl) dichloroacetamide, N-(2,4-dichlorobenzyD-N-(Z ethoxyethyl) dichlo-roacetamide, N-(4-n-butoxybenzyD-N-(2- ethoxyethyl)dichloroacetamide and N (3,4 dichlorobenzyl)-N-(3-ethoxypropyl) dichl'oroacetamide, have ED valuesbelow 25 mg. per kg. of body weight, ED meaning the eifective dose necessary to clear 50% of the hamsters of the amebic infection.

This application is a division of my copending application Serial No. 411,554, filed February 19, 1954, now U. S. Patent No. 2,732,403, issued January 24, 1946.

I claim:

1. A compound having the formula where Ar is a member selected from the group consisting of phenyl, naphthyl, biphenylyl, furyl, pyridyl and thienyl radicals and such radicals substituted by from one to three substituents selected from the group consisting of halo, lower alkoxy, lower alkyl, lower alkylmercapto, lower alkylsulfonyl, nitro and di(lower alkyl)amino, X is a lower alkylene radical having one to four carbon atoms, Y is a lower alkylene radical having two to six carbon atoms and having its two free valence bonds on different carbon atoms and R is a hydrocarbyl radical having from one to eight carbon atoms.

2. A compound having the formula where Ar is a phenyl radical substituted by from one to three halo radicals, Y is a lower alkylene radical having two to six carbon atoms and having its two free valence bonds on different carbon atoms and R is a lower alkyl radical having one to eight carbon atoms.

3. A compound having the formula (halogen) CH2'NHCH2CH:O-R

(halogen) where R is a lower alk-yl radical having one to eight carbon atoms.

4. A compound having the formula (lower alkyl) CHz-NHCH1CHzO-R where R is a lower alkyl radical having one to eight carbon atoms.v

a 10 5. A compound having the formula where R is a lower alkyl radical having one to eight carbon atoms. 7. N-(Z-ethoxyethyl)-3,4-dichlorobenzylamine.

where Ar 1s a phenyl radical substltuted by from one to three lower alkoxy radicals, Y is a lower alkylene radical 5 fi' g' g f fi g'i f i g i g having two to six carbon atoms and having its two free b i f 1' 1c elllzy l valence bonds on difierent carbon atoms and R is a lower E .utoxy fi i alkyl radical having one to eight carbon atoms. oxye y 'lsopmpy enzy amme' A compound having the formula References Cited in the file of this patent (lower alky1)-O 10 Beilstein: vol. XII, 1st supplement, page 455. CHr-NH-CHzCHz-O-R 

1. A COMPOUND HAVING THE FORMULA 